BRPI0613644A2 - moduladores de tieno pirimidina e tieno pirimidina cinase - Google Patents

moduladores de tieno pirimidina e tieno pirimidina cinase Download PDF

Info

Publication number: BRPI0613644A2
Authority: BR; Brazil
Prior art keywords: formula; compound; alkyl; original document; see original
Prior art date: 2005-06-10

Application number

BRPI0613644-3A

Other languages

English (en)

Portuguese (pt)

Inventor

Michael David Gaul

Kevin Douglas Kreutter

Christian Andrew Baumann

Original Assignee

Janssen Pharmaceutica Nv

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-06-10

Filing date

2006-06-07

Publication date

2011-01-25

2006-06-07 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

2011-01-25 Publication of BRPI0613644A2 publication Critical patent/BRPI0613644A2/pt

Links

108091000080 Phosphotransferase Proteins 0.000 title abstract description 16
102000020233 phosphotransferase Human genes 0.000 title abstract description 16
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 246
101000932478 Homo sapiens Receptor-type tyrosine-protein kinase FLT3 Proteins 0.000 claims abstract description 96
102100020718 Receptor-type tyrosine-protein kinase FLT3 Human genes 0.000 claims abstract description 95
238000000034 method Methods 0.000 claims abstract description 89
230000008569 process Effects 0.000 claims abstract description 57
230000000694 effects Effects 0.000 claims abstract description 24
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
230000002062 proliferating effect Effects 0.000 claims abstract description 19
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
-1 pyrrolidinonyl Chemical group 0.000 claims description 173
125000000217 alkyl group Chemical group 0.000 claims description 98
125000001072 heteroaryl group Chemical group 0.000 claims description 43
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 41
239000000523 sample Substances 0.000 claims description 36
125000000753 cycloalkyl group Chemical group 0.000 claims description 32
125000003118 aryl group Chemical group 0.000 claims description 31
125000001424 substituent group Chemical group 0.000 claims description 31
125000000623 heterocyclic group Chemical group 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 27
229910052757 nitrogen Inorganic materials 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 24
150000002367 halogens Chemical class 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 23
125000003282 alkyl amino group Chemical group 0.000 claims description 23
239000003814 drug Substances 0.000 claims description 21
125000003342 alkenyl group Chemical group 0.000 claims description 18
125000004663 dialkyl amino group Chemical group 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 17
239000002246 antineoplastic agent Substances 0.000 claims description 15
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
229940127089 cytotoxic agent Drugs 0.000 claims description 14
239000003937 drug carrier Substances 0.000 claims description 14
125000004475 heteroaralkyl group Chemical group 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000005605 benzo group Chemical group 0.000 claims description 11
239000003153 chemical reaction reagent Substances 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
150000001204 N-oxides Chemical class 0.000 claims description 8
239000007844 bleaching agent Substances 0.000 claims description 8
239000003054 catalyst Substances 0.000 claims description 8
125000004122 cyclic group Chemical group 0.000 claims description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
229910052763 palladium Inorganic materials 0.000 claims description 7
238000001959 radiotherapy Methods 0.000 claims description 7
238000001415 gene therapy Methods 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
230000008878 coupling Effects 0.000 claims description 5
238000010168 coupling process Methods 0.000 claims description 5
238000005859 coupling reaction Methods 0.000 claims description 5
238000009169 immunotherapy Methods 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
125000004001 thioalkyl group Chemical group 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
238000013270 controlled release Methods 0.000 claims 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 52
238000011282 treatment Methods 0.000 abstract description 32
206010028980 Neoplasm Diseases 0.000 abstract description 23
239000003112 inhibitor Substances 0.000 abstract description 12
108090000412 Protein-Tyrosine Kinases Proteins 0.000 abstract description 4
102000004022 Protein-Tyrosine Kinases Human genes 0.000 abstract description 4
150000003222 pyridines Chemical class 0.000 abstract description 4
230000002265 prevention Effects 0.000 abstract description 3
150000003230 pyrimidines Chemical class 0.000 abstract description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 59
210000004027 cell Anatomy 0.000 description 59
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 54
239000000203 mixture Substances 0.000 description 42
238000005160 1H NMR spectroscopy Methods 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 38
208000035475 disorder Diseases 0.000 description 38
239000000243 solution Substances 0.000 description 37
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
239000003795 chemical substances by application Substances 0.000 description 23
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
230000005764 inhibitory process Effects 0.000 description 20
125000001544 thienyl group Chemical group 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 17
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
239000012044 organic layer Substances 0.000 description 16
239000007787 solid Substances 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
235000019441 ethanol Nutrition 0.000 description 15
230000035772 mutation Effects 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
229910052799 carbon Inorganic materials 0.000 description 14
235000019439 ethyl acetate Nutrition 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
125000002541 furyl group Chemical group 0.000 description 13
239000003826 tablet Substances 0.000 description 13
125000000335 thiazolyl group Chemical group 0.000 description 13
TWTODSLDHCDLDR-UHFFFAOYSA-N 4-chlorothieno[3,2-d]pyrimidine Chemical compound ClC1=NC=NC2=C1SC=C2 TWTODSLDHCDLDR-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
125000004429 atom Chemical group 0.000 description 12
229940079593 drug Drugs 0.000 description 12
150000002148 esters Chemical class 0.000 description 12
125000002971 oxazolyl group Chemical group 0.000 description 12
108020003175 receptors Proteins 0.000 description 12
102000005962 receptors Human genes 0.000 description 12
239000002253 acid Substances 0.000 description 11
239000002775 capsule Substances 0.000 description 11
150000001721 carbon Chemical group 0.000 description 11
201000010099 disease Diseases 0.000 description 11
125000002883 imidazolyl group Chemical group 0.000 description 11
125000000168 pyrrolyl group Chemical group 0.000 description 11
150000003254 radicals Chemical class 0.000 description 11
238000002560 therapeutic procedure Methods 0.000 description 11
208000031261 Acute myeloid leukaemia Diseases 0.000 description 10
201000003793 Myelodysplastic syndrome Diseases 0.000 description 10
239000000460 chlorine Substances 0.000 description 10
230000008685 targeting Effects 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
239000010410 layer Substances 0.000 description 9
208000032839 leukemia Diseases 0.000 description 9
108090000623 proteins and genes Proteins 0.000 description 9
125000000714 pyrimidinyl group Chemical group 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000007921 spray Substances 0.000 description 9
208000033776 Myeloid Acute Leukemia Diseases 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
238000003818 flash chromatography Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
125000006239 protecting group Chemical group 0.000 description 8
238000000746 purification Methods 0.000 description 8
125000003373 pyrazinyl group Chemical group 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
239000000725 suspension Substances 0.000 description 8
239000003981 vehicle Substances 0.000 description 8
NZCRUBBNZGVREM-UHFFFAOYSA-N 4-chlorothieno[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=CS2 NZCRUBBNZGVREM-UHFFFAOYSA-N 0.000 description 7
206010035226 Plasma cell myeloma Diseases 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
239000002585 base Substances 0.000 description 7
125000002619 bicyclic group Chemical group 0.000 description 7
230000037396 body weight Effects 0.000 description 7
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 7
238000003756 stirring Methods 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
208000002250 Hematologic Neoplasms Diseases 0.000 description 6
108010002386 Interleukin-3 Proteins 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000008280 blood Substances 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
230000004663 cell proliferation Effects 0.000 description 6
238000000576 coating method Methods 0.000 description 6
238000011161 development Methods 0.000 description 6
230000018109 developmental process Effects 0.000 description 6
230000014509 gene expression Effects 0.000 description 6
239000003102 growth factor Substances 0.000 description 6
229960004592 isopropanol Drugs 0.000 description 6
239000007788 liquid Substances 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
229940002612 prodrug Drugs 0.000 description 6
239000000651 prodrug Substances 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
150000003573 thiols Chemical class 0.000 description 6
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
208000014697 Acute lymphocytic leukaemia Diseases 0.000 description 5
208000033766 Prolymphocytic Leukemia Diseases 0.000 description 5
230000006978 adaptation Effects 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
239000000969 carrier Substances 0.000 description 5
230000010261 cell growth Effects 0.000 description 5
230000001419 dependent effect Effects 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
239000012065 filter cake Substances 0.000 description 5
239000012467 final product Substances 0.000 description 5
230000012010 growth Effects 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
239000003921 oil Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 5
239000006187 pill Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
208000003476 primary myelofibrosis Diseases 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
210000000130 stem cell Anatomy 0.000 description 5
210000004881 tumor cell Anatomy 0.000 description 5
BECYHNUAQZIOFD-UHFFFAOYSA-N (4-nitrophenyl) n-(4-morpholin-4-ylphenyl)carbamate;hydrochloride Chemical compound Cl.C1=CC([N+](=O)[O-])=CC=C1OC(=O)NC1=CC=C(N2CCOCC2)C=C1 BECYHNUAQZIOFD-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
208000024893 Acute lymphoblastic leukemia Diseases 0.000 description 4
208000036762 Acute promyelocytic leukaemia Diseases 0.000 description 4
XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 4
239000004215 Carbon black (E152) Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
208000010833 Chronic myeloid leukaemia Diseases 0.000 description 4
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 4
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
208000032027 Essential Thrombocythemia Diseases 0.000 description 4
208000017604 Hodgkin disease Diseases 0.000 description 4
208000010747 Hodgkins lymphoma Diseases 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 4
208000037538 Myelomonocytic Juvenile Leukemia Diseases 0.000 description 4
208000014767 Myeloproliferative disease Diseases 0.000 description 4
208000033755 Neutrophilic Chronic Leukemia Diseases 0.000 description 4
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 description 4
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
208000017733 acquired polycythemia vera Diseases 0.000 description 4
RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000000427 antigen Substances 0.000 description 4
102000036639 antigens Human genes 0.000 description 4
108091007433 antigens Proteins 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
238000002512 chemotherapy Methods 0.000 description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
201000010903 chronic neutrophilic leukemia Diseases 0.000 description 4
238000012377 drug delivery Methods 0.000 description 4
239000012634 fragment Substances 0.000 description 4
230000011132 hemopoiesis Effects 0.000 description 4
239000012456 homogeneous solution Substances 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
201000005992 juvenile myelomonocytic leukemia Diseases 0.000 description 4
239000003446 ligand Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000011159 matrix material Substances 0.000 description 4
206010028537 myelofibrosis Diseases 0.000 description 4
201000000050 myeloid neoplasm Diseases 0.000 description 4
230000001613 neoplastic effect Effects 0.000 description 4
239000012038 nucleophile Substances 0.000 description 4
230000003647 oxidation Effects 0.000 description 4
230000026731 phosphorylation Effects 0.000 description 4
238000006366 phosphorylation reaction Methods 0.000 description 4
208000037244 polycythemia vera Diseases 0.000 description 4
230000035755 proliferation Effects 0.000 description 4
235000018102 proteins Nutrition 0.000 description 4
102000004169 proteins and genes Human genes 0.000 description 4
208000037803 restenosis Diseases 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
229940124530 sulfonamide Drugs 0.000 description 4
239000000375 suspending agent Substances 0.000 description 4
229940121358 tyrosine kinase inhibitor Drugs 0.000 description 4
239000005483 tyrosine kinase inhibitor Substances 0.000 description 4
230000002792 vascular Effects 0.000 description 4
229920002554 vinyl polymer Polymers 0.000 description 4
MXQSURPDIPQWQD-UHFFFAOYSA-N (4-pyrrolidin-1-ylphenyl)carbamic acid Chemical compound C1=CC(NC(=O)O)=CC=C1N1CCCC1 MXQSURPDIPQWQD-UHFFFAOYSA-N 0.000 description 3
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
PNBUGOFIKAHZRW-UHFFFAOYSA-N 1-isocyanato-4-phenoxybenzene Chemical compound C1=CC(N=C=O)=CC=C1OC1=CC=CC=C1 PNBUGOFIKAHZRW-UHFFFAOYSA-N 0.000 description 3
CKZKDUMVKHYMSG-UHFFFAOYSA-N 1-thieno[2,3-d]pyrimidin-4-ylpiperidin-4-ol Chemical compound C1CC(O)CCN1C1=NC=NC2=C1C=CS2 CKZKDUMVKHYMSG-UHFFFAOYSA-N 0.000 description 3
ZKHJFNLBXWYJGF-UHFFFAOYSA-N 1-thieno[3,2-d]pyrimidin-4-ylpyrrolidin-3-amine;hydrochloride Chemical compound Cl.C1C(N)CCN1C1=NC=NC2=C1SC=C2 ZKHJFNLBXWYJGF-UHFFFAOYSA-N 0.000 description 3
CMIXHHOZGMSYKN-UHFFFAOYSA-N 6-bromo-4-chlorothieno[2,3-d]pyrimidine Chemical compound ClC1=NC=NC2=C1C=C(Br)S2 CMIXHHOZGMSYKN-UHFFFAOYSA-N 0.000 description 3
RJKAKJGOZXERRE-UHFFFAOYSA-N 6-bromo-4-chlorothieno[3,2-d]pyrimidine Chemical compound ClC1=NC=NC2=C1SC(Br)=C2 RJKAKJGOZXERRE-UHFFFAOYSA-N 0.000 description 3
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
206010073478 Anaplastic large-cell lymphoma Diseases 0.000 description 3
241000416162 Astragalus gummifer Species 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
206010008583 Chloroma Diseases 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
UIARLYUEJFELEN-LROUJFHJSA-N LSM-1231 Chemical compound C12=C3N4C5=CC=CC=C5C3=C3C(=O)NCC3=C2C2=CC=CC=C2N1[C@]1(C)[C@](CO)(O)C[C@H]4O1 UIARLYUEJFELEN-LROUJFHJSA-N 0.000 description 3
208000032004 Large-Cell Anaplastic Lymphoma Diseases 0.000 description 3
235000010643 Leucaena leucocephala Nutrition 0.000 description 3
240000007472 Leucaena leucocephala Species 0.000 description 3
206010025323 Lymphomas Diseases 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
208000034578 Multiple myelomas Diseases 0.000 description 3
241001529936 Murinae Species 0.000 description 3
101100335081 Mus musculus Flt3 gene Proteins 0.000 description 3
229910019142 PO4 Inorganic materials 0.000 description 3
108010001441 Phosphopeptides Proteins 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
208000033826 Promyelocytic Acute Leukemia Diseases 0.000 description 3
102000001253 Protein Kinase Human genes 0.000 description 3
206010037211 Psychomotor hyperactivity Diseases 0.000 description 3
NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 3
229920001615 Tragacanth Polymers 0.000 description 3
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
208000036676 acute undifferentiated leukemia Diseases 0.000 description 3
125000000304 alkynyl group Chemical group 0.000 description 3
238000010171 animal model Methods 0.000 description 3
230000000259 anti-tumor effect Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
229940060038 chlorine Drugs 0.000 description 3
229960004316 cisplatin Drugs 0.000 description 3
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
238000001816 cooling Methods 0.000 description 3
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 3
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 3
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 3
YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 3
230000006870 function Effects 0.000 description 3
230000009036 growth inhibition Effects 0.000 description 3
208000018706 hematopoietic system disease Diseases 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
125000005647 linker group Chemical group 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
239000000314 lubricant Substances 0.000 description 3
229920000609 methyl cellulose Polymers 0.000 description 3
239000001923 methylcellulose Substances 0.000 description 3
235000010981 methylcellulose Nutrition 0.000 description 3
201000005987 myeloid sarcoma Diseases 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
238000011275 oncology therapy Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
230000008506 pathogenesis Effects 0.000 description 3
235000021317 phosphate Nutrition 0.000 description 3
239000010452 phosphate Substances 0.000 description 3
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
108060006633 protein kinase Proteins 0.000 description 3
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 3
125000000719 pyrrolidinyl group Chemical group 0.000 description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
230000004044 response Effects 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
241000894007 species Species 0.000 description 3
239000008107 starch Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
235000000346 sugar Nutrition 0.000 description 3
150000003456 sulfonamides Chemical class 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
229940124597 therapeutic agent Drugs 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
235000010487 tragacanth Nutrition 0.000 description 3
239000000196 tragacanth Substances 0.000 description 3
229940116362 tragacanth Drugs 0.000 description 3
229960004418 trolamine Drugs 0.000 description 3
LGPWSGRWCMAMFH-UHFFFAOYSA-N (1-thieno[2,3-d]pyrimidin-4-ylpiperidin-4-yl) n-(4-propan-2-ylphenyl)carbamate Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)OC1CCN(C=2C=3C=CSC=3N=CN=2)CC1 LGPWSGRWCMAMFH-UHFFFAOYSA-N 0.000 description 2
REKJTGWHCUWING-UHFFFAOYSA-N (1-thieno[2,3-d]pyrimidin-4-ylpyrrolidin-3-yl) n-(4-propan-2-ylphenyl)carbamate Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)OC1CN(C=2C=3C=CSC=3N=CN=2)CC1 REKJTGWHCUWING-UHFFFAOYSA-N 0.000 description 2
LSHMLUZVIBKADU-UHFFFAOYSA-N (4-propan-2-ylphenyl)carbamic acid Chemical compound CC(C)C1=CC=C(NC(O)=O)C=C1 LSHMLUZVIBKADU-UHFFFAOYSA-N 0.000 description 2
IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
108091032973 (ribonucleotides)n+m Proteins 0.000 description 2
UXRXWRRIXGUJHG-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpyrrolidin-3-yl)urea Chemical compound C1CN(C=2C=3SC=CC=3N=CN=2)CC1NC(=O)NC(C=C1)=CC=C1C1CCCCC1 UXRXWRRIXGUJHG-UHFFFAOYSA-N 0.000 description 2
UXLUWKVRWMVVIT-UHFFFAOYSA-N 1-(4-phenoxyphenyl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpyrrolidin-3-yl)urea Chemical compound C1CN(C=2C=3SC=CC=3N=CN=2)CC1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 UXLUWKVRWMVVIT-UHFFFAOYSA-N 0.000 description 2
LKOOPCITYQDWEB-UHFFFAOYSA-N 1-(4-pyrrolidin-1-ylphenyl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpyrrolidin-3-yl)urea Chemical compound C1CN(C=2C=3SC=CC=3N=CN=2)CC1NC(=O)NC(C=C1)=CC=C1N1CCCC1 LKOOPCITYQDWEB-UHFFFAOYSA-N 0.000 description 2
GGGJCHLCRBZDOS-UHFFFAOYSA-N 1-(6-cyclobutyloxypyridin-3-yl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpiperidin-4-yl)urea Chemical compound C1CN(C=2C=3SC=CC=3N=CN=2)CCC1NC(=O)NC(C=N1)=CC=C1OC1CCC1 GGGJCHLCRBZDOS-UHFFFAOYSA-N 0.000 description 2
GKTNGVKXNAICDC-UHFFFAOYSA-N 1-[4-(diethylamino)phenyl]-3-(1-thieno[3,2-d]pyrimidin-4-ylpyrrolidin-3-yl)urea Chemical compound C1=CC(N(CC)CC)=CC=C1NC(=O)NC1CN(C=2C=3SC=CC=3N=CN=2)CC1 GKTNGVKXNAICDC-UHFFFAOYSA-N 0.000 description 2
WTFIZQHVJMNEEZ-UHFFFAOYSA-N 1-thieno[3,2-d]pyrimidin-4-ylpyrrolidin-3-ol Chemical compound C1C(O)CCN1C1=NC=NC2=C1SC=C2 WTFIZQHVJMNEEZ-UHFFFAOYSA-N 0.000 description 2
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 2
ABNRSCLPSNNUNA-UHFFFAOYSA-N 2-cyclobutyloxy-5-nitropyridine Chemical compound N1=CC([N+](=O)[O-])=CC=C1OC1CCC1 ABNRSCLPSNNUNA-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
229960000549 4-dimethylaminophenol Drugs 0.000 description 2
MLNFMFAMNBGAQT-UHFFFAOYSA-N 4-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=C(N)C=C1 MLNFMFAMNBGAQT-UHFFFAOYSA-N 0.000 description 2
JRBXTNBZQGKGBX-UHFFFAOYSA-N 6-cyclobutyloxypyridin-3-amine Chemical compound N1=CC(N)=CC=C1OC1CCC1 JRBXTNBZQGKGBX-UHFFFAOYSA-N 0.000 description 2
208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 description 2
208000003950 B-cell lymphoma Diseases 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
229940127291 Calcium channel antagonist Drugs 0.000 description 2
GAGWJHPBXLXJQN-UORFTKCHSA-N Capecitabine Chemical compound C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1[C@H]1[C@H](O)[C@H](O)[C@@H](C)O1 GAGWJHPBXLXJQN-UORFTKCHSA-N 0.000 description 2
GAGWJHPBXLXJQN-UHFFFAOYSA-N Capecitabine Natural products C1=C(F)C(NC(=O)OCCCCC)=NC(=O)N1C1C(O)C(O)C(C)O1 GAGWJHPBXLXJQN-UHFFFAOYSA-N 0.000 description 2
208000024172 Cardiovascular disease Diseases 0.000 description 2
DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
108010092160 Dactinomycin Proteins 0.000 description 2
238000002965 ELISA Methods 0.000 description 2
102100020715 Fms-related tyrosine kinase 3 ligand protein Human genes 0.000 description 2
101710162577 Fms-related tyrosine kinase 3 ligand protein Proteins 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
208000021519 Hodgkin lymphoma Diseases 0.000 description 2
101100335080 Homo sapiens FLT3 gene Proteins 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
206010028561 Myeloid metaplasia Diseases 0.000 description 2
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 2
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 2
229930012538 Paclitaxel Natural products 0.000 description 2
206010033661 Pancytopenia Diseases 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
239000012980 RPMI-1640 medium Substances 0.000 description 2
108020004459 Small interfering RNA Proteins 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
208000029052 T-cell acute lymphoblastic leukemia Diseases 0.000 description 2
208000005485 Thrombocytosis Diseases 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 2
229940122803 Vinca alkaloid Drugs 0.000 description 2
CXQJJTNMUFBTON-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)N(C(O)=O)C=1C=NC(=CC1)OC1CCC1 Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)N(C(O)=O)C=1C=NC(=CC1)OC1CCC1 CXQJJTNMUFBTON-UHFFFAOYSA-N 0.000 description 2
JLFVIEQMRKMAIT-UHFFFAOYSA-N ac1l9mnz Chemical group O.O.O JLFVIEQMRKMAIT-UHFFFAOYSA-N 0.000 description 2
RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
239000000654 additive Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
125000005157 alkyl carboxy group Chemical group 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
229960002932 anastrozole Drugs 0.000 description 2
YBBLVLTVTVSKRW-UHFFFAOYSA-N anastrozole Chemical compound N#CC(C)(C)C1=CC(C(C)(C#N)C)=CC(CN2N=CN=C2)=C1 YBBLVLTVTVSKRW-UHFFFAOYSA-N 0.000 description 2
238000002399 angioplasty Methods 0.000 description 2
125000000129 anionic group Chemical group 0.000 description 2
229940045799 anthracyclines and related substance Drugs 0.000 description 2
229940045985 antineoplastic platinum compound Drugs 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
210000001367 artery Anatomy 0.000 description 2
238000003556 assay Methods 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
239000000560 biocompatible material Substances 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
210000001185 bone marrow Anatomy 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
229960005069 calcium Drugs 0.000 description 2
239000000480 calcium channel blocker Substances 0.000 description 2
VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
229960004117 capecitabine Drugs 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
229960005243 carmustine Drugs 0.000 description 2
125000002091 cationic group Chemical group 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
238000011281 clinical therapy Methods 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
239000003086 colorant Substances 0.000 description 2
238000002648 combination therapy Methods 0.000 description 2
125000000392 cycloalkenyl group Chemical group 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
229960004397 cyclophosphamide Drugs 0.000 description 2
208000024389 cytopenia Diseases 0.000 description 2
229960000640 dactinomycin Drugs 0.000 description 2
230000006378 damage Effects 0.000 description 2
229960000975 daunorubicin Drugs 0.000 description 2
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
230000002950 deficient Effects 0.000 description 2
210000004443 dendritic cell Anatomy 0.000 description 2
238000013461 design Methods 0.000 description 2
238000001514 detection method Methods 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
238000009792 diffusion process Methods 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
235000011180 diphosphates Nutrition 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
229960003668 docetaxel Drugs 0.000 description 2
229960004679 doxorubicin Drugs 0.000 description 2
239000012055 enteric layer Substances 0.000 description 2
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 2
229960005420 etoposide Drugs 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
108700014844 flt3 ligand Proteins 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000007789 gas Substances 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 description 2
229960005277 gemcitabine Drugs 0.000 description 2
150000004676 glycans Chemical class 0.000 description 2
239000008187 granular material Substances 0.000 description 2
125000005553 heteroaryloxy group Chemical group 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
230000001900 immune effect Effects 0.000 description 2
238000002513 implantation Methods 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
125000001041 indolyl group Chemical group 0.000 description 2
230000003834 intracellular effect Effects 0.000 description 2
UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 description 2
229960004768 irinotecan Drugs 0.000 description 2
238000000021 kinase assay Methods 0.000 description 2
230000000670 limiting effect Effects 0.000 description 2
239000002502 liposome Substances 0.000 description 2
239000006166 lysate Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
230000003211 malignant effect Effects 0.000 description 2
BMGQWWVMWDBQGC-IIFHNQTCSA-N midostaurin Chemical compound CN([C@H]1[C@H]([C@]2(C)O[C@@H](N3C4=CC=CC=C4C4=C5C(=O)NCC5=C5C6=CC=CC=C6N2C5=C43)C1)OC)C(=O)C1=CC=CC=C1 BMGQWWVMWDBQGC-IIFHNQTCSA-N 0.000 description 2
229950010895 midostaurin Drugs 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
210000000822 natural killer cell Anatomy 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
150000003833 nucleoside derivatives Chemical class 0.000 description 2
239000007764 o/w emulsion Substances 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229960001592 paclitaxel Drugs 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 2
239000008177 pharmaceutical agent Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000012071 phase Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 2
125000004193 piperazinyl group Chemical group 0.000 description 2
125000003386 piperidinyl group Chemical group 0.000 description 2
150000003058 platinum compounds Chemical class 0.000 description 2
229920001490 poly(butyl methacrylate) polymer Polymers 0.000 description 2
229920001282 polysaccharide Polymers 0.000 description 2
239000005017 polysaccharide Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
229960004919 procaine Drugs 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
108091008598 receptor tyrosine kinases Proteins 0.000 description 2
102000027426 receptor tyrosine kinases Human genes 0.000 description 2
230000009467 reduction Effects 0.000 description 2
206010039073 rheumatoid arthritis Diseases 0.000 description 2
125000006413 ring segment Chemical group 0.000 description 2
238000005488 sandblasting Methods 0.000 description 2
239000004055 small Interfering RNA Substances 0.000 description 2
150000003384 small molecules Chemical class 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229940083542 sodium Drugs 0.000 description 2
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 2
125000006850 spacer group Chemical group 0.000 description 2
239000008174 sterile solution Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
150000008163 sugars Chemical class 0.000 description 2
150000003462 sulfoxides Chemical class 0.000 description 2
239000000829 suppository Substances 0.000 description 2
238000013268 sustained release Methods 0.000 description 2
239000012730 sustained-release form Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
208000011580 syndromic disease Diseases 0.000 description 2
229960001603 tamoxifen Drugs 0.000 description 2
UXXQOJXBIDBUAC-UHFFFAOYSA-N tandutinib Chemical compound COC1=CC2=C(N3CCN(CC3)C(=O)NC=3C=CC(OC(C)C)=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 UXXQOJXBIDBUAC-UHFFFAOYSA-N 0.000 description 2
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 2
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 2
NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 2
229960001278 teniposide Drugs 0.000 description 2
125000004568 thiomorpholinyl group Chemical group 0.000 description 2
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 2
229960000303 topotecan Drugs 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
229960000575 trastuzumab Drugs 0.000 description 2
125000001425 triazolyl group Chemical group 0.000 description 2
229940086542 triethylamine Drugs 0.000 description 2
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
230000005748 tumor development Effects 0.000 description 2
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 2
239000002691 unilamellar liposome Substances 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
210000005166 vasculature Anatomy 0.000 description 2
229960001722 verapamil Drugs 0.000 description 2
229960003048 vinblastine Drugs 0.000 description 2
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 2
GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 2
229960002066 vinorelbine Drugs 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
NBQMEEYTKZVMBY-UHFFFAOYSA-N (1-thieno[2,3-d]pyrimidin-4-ylpiperidin-4-yl) n-(4-propan-2-yloxyphenyl)carbamate Chemical compound C1=CC(OC(C)C)=CC=C1NC(=O)OC1CCN(C=2C=3C=CSC=3N=CN=2)CC1 NBQMEEYTKZVMBY-UHFFFAOYSA-N 0.000 description 1
GYUHVJIZPOHCEZ-UHFFFAOYSA-N (1-thieno[3,2-d]pyrimidin-4-ylpiperidin-4-yl) n-(4-propan-2-yloxyphenyl)carbamate Chemical compound C1=CC(OC(C)C)=CC=C1NC(=O)OC1CCN(C=2C=3SC=CC=3N=CN=2)CC1 GYUHVJIZPOHCEZ-UHFFFAOYSA-N 0.000 description 1
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
MHFUWOIXNMZFIW-WNQIDUERSA-N (2s)-2-hydroxypropanoic acid;n-[4-[4-(4-methylpiperazin-1-yl)-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyrimidin-2-yl]sulfanylphenyl]cyclopropanecarboxamide Chemical compound C[C@H](O)C(O)=O.C1CN(C)CCN1C1=CC(NC2=NNC(C)=C2)=NC(SC=2C=CC(NC(=O)C3CC3)=CC=2)=N1 MHFUWOIXNMZFIW-WNQIDUERSA-N 0.000 description 1
DMQYDVBIPXAAJA-VHXPQNKSSA-N (3z)-5-[(1-ethylpiperidin-4-yl)amino]-3-[(3-fluorophenyl)-(5-methyl-1h-imidazol-2-yl)methylidene]-1h-indol-2-one Chemical compound C1CN(CC)CCC1NC1=CC=C(NC(=O)\C2=C(/C=3NC=C(C)N=3)C=3C=C(F)C=CC=3)C2=C1 DMQYDVBIPXAAJA-VHXPQNKSSA-N 0.000 description 1
ARIOIRXTWLTVPY-UHFFFAOYSA-N (4-ethylphenyl)carbamic acid Chemical compound CCC1=CC=C(NC(O)=O)C=C1 ARIOIRXTWLTVPY-UHFFFAOYSA-N 0.000 description 1
CKXNBVOEYVTESJ-UHFFFAOYSA-N (4-nitrophenyl) n-(6-cyclobutyloxypyridin-3-yl)carbamate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)NC(C=N1)=CC=C1OC1CCC1 CKXNBVOEYVTESJ-UHFFFAOYSA-N 0.000 description 1
ZHCHVKBBSUIADI-UHFFFAOYSA-N (4-nitrophenyl) n-[4-(diethylamino)phenyl]carbamate;hydrochloride Chemical compound Cl.C1=CC(N(CC)CC)=CC=C1NC(=O)OC1=CC=C([N+]([O-])=O)C=C1 ZHCHVKBBSUIADI-UHFFFAOYSA-N 0.000 description 1
FSMDIXFTJVXPHR-UHFFFAOYSA-N (4-propan-2-yloxyphenyl)carbamic acid Chemical compound CC(C)OC1=CC=C(NC(O)=O)C=C1 FSMDIXFTJVXPHR-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 description 1
125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 description 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 1
FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
JPRPJUMQRZTTED-UHFFFAOYSA-N 1,3-dioxolanyl Chemical group [CH]1OCCO1 JPRPJUMQRZTTED-UHFFFAOYSA-N 0.000 description 1
125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 description 1
UBHJQQKPWPDYNB-UHFFFAOYSA-N 1-(4-bromophenyl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpyrrolidin-3-yl)urea Chemical compound C1=CC(Br)=CC=C1NC(=O)NC1CN(C=2C=3SC=CC=3N=CN=2)CC1 UBHJQQKPWPDYNB-UHFFFAOYSA-N 0.000 description 1
IRJURHKTZPDBFV-UHFFFAOYSA-N 1-(4-cyclohexylphenyl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpiperidin-4-yl)urea Chemical compound C1CN(C=2C=3SC=CC=3N=CN=2)CCC1NC(=O)NC(C=C1)=CC=C1C1CCCCC1 IRJURHKTZPDBFV-UHFFFAOYSA-N 0.000 description 1
OSDVVVRCULZOGY-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpiperidin-4-yl)urea Chemical compound C1CN(C=2C=3SC=CC=3N=CN=2)CCC1NC(=O)NC(C=C1)=CC=C1N1CCOCC1 OSDVVVRCULZOGY-UHFFFAOYSA-N 0.000 description 1
BLQAELNKKMDYSG-UHFFFAOYSA-N 1-(4-morpholin-4-ylphenyl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpyrrolidin-3-yl)urea Chemical compound C1CN(C=2C=3SC=CC=3N=CN=2)CC1NC(=O)NC(C=C1)=CC=C1N1CCOCC1 BLQAELNKKMDYSG-UHFFFAOYSA-N 0.000 description 1
XDJDUEFWVZYHBS-UHFFFAOYSA-N 1-(4-phenoxyphenyl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpiperidin-4-yl)urea Chemical compound C1CN(C=2C=3SC=CC=3N=CN=2)CCC1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 XDJDUEFWVZYHBS-UHFFFAOYSA-N 0.000 description 1
GBQQXBZQMCXXKQ-UHFFFAOYSA-N 1-(4-propan-2-yloxyphenyl)-3-(1-thieno[2,3-d]pyrimidin-4-ylpyrrolidin-3-yl)urea Chemical compound C1=CC(OC(C)C)=CC=C1NC(=O)NC1CN(C=2C=3C=CSC=3N=CN=2)CC1 GBQQXBZQMCXXKQ-UHFFFAOYSA-N 0.000 description 1
ZJTSYBNTJSMVSC-UHFFFAOYSA-N 1-(4-propan-2-ylphenyl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpyrrolidin-3-yl)urea Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)NC1CN(C=2C=3SC=CC=3N=CN=2)CC1 ZJTSYBNTJSMVSC-UHFFFAOYSA-N 0.000 description 1
HCKGJZIHHPSVPQ-UHFFFAOYSA-N 1-(4-pyrrolidin-1-ylphenyl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpiperidin-4-yl)urea Chemical compound C1CN(C=2C=3SC=CC=3N=CN=2)CCC1NC(=O)NC(C=C1)=CC=C1N1CCCC1 HCKGJZIHHPSVPQ-UHFFFAOYSA-N 0.000 description 1
ROBVPFHJYWACQW-UHFFFAOYSA-N 1-(6-cyclobutyloxypyridin-3-yl)-3-(1-thieno[3,2-d]pyrimidin-4-ylpyrrolidin-3-yl)urea Chemical compound C1CN(C=2C=3SC=CC=3N=CN=2)CC1NC(=O)NC(C=N1)=CC=C1OC1CCC1 ROBVPFHJYWACQW-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
AWNXKZVIZARMME-UHFFFAOYSA-N 1-[[5-[2-[(2-chloropyridin-4-yl)amino]pyrimidin-4-yl]-4-(cyclopropylmethyl)pyrimidin-2-yl]amino]-2-methylpropan-2-ol Chemical compound N=1C(NCC(C)(O)C)=NC=C(C=2N=C(NC=3C=C(Cl)N=CC=3)N=CC=2)C=1CC1CC1 AWNXKZVIZARMME-UHFFFAOYSA-N 0.000 description 1
CZQIJQFTRGDODI-UHFFFAOYSA-N 1-bromo-4-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C=C1 CZQIJQFTRGDODI-UHFFFAOYSA-N 0.000 description 1
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
YSNJGLHAGQOFFP-UHFFFAOYSA-N 1-nitroethanone Chemical class CC(=O)[N+]([O-])=O YSNJGLHAGQOFFP-UHFFFAOYSA-N 0.000 description 1
QYCKVZZMAXDBHQ-UHFFFAOYSA-N 1-piperidin-4-ylbenzimidazole Chemical class C1CNCCC1N1C2=CC=CC=C2N=C1 QYCKVZZMAXDBHQ-UHFFFAOYSA-N 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical group COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
DVSHSUYCVKEMSL-UHFFFAOYSA-N 2-bromothieno[3,2-d]pyrimidine Chemical compound BrC1=NC=C2SC=CC2=N1 DVSHSUYCVKEMSL-UHFFFAOYSA-N 0.000 description 1
BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical compound C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 description 1
POWOVNFCLDRNMS-UHFFFAOYSA-N 2h-furan-2-ide Chemical compound C=1C=[C-]OC=1 POWOVNFCLDRNMS-UHFFFAOYSA-N 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
DZQLVVLATXPWBK-UHFFFAOYSA-N 3-phenyl-1H-benzofuro[3,2-c]pyrazole Chemical compound C1=CC=CC=C1C1=NNC2=C1OC1=CC=CC=C12 DZQLVVLATXPWBK-UHFFFAOYSA-N 0.000 description 1
125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 description 1
XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical compound OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 description 1
QDPVYZNVVQQULH-UHFFFAOYSA-N 4-amino-5-fluoro-3-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-quinolin-2-one 2-hydroxypropanoic acid hydrate Chemical compound O.CC(O)C(O)=O.C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C(NC4=CC=CC(F)=C4C=3N)=O)C2=C1 QDPVYZNVVQQULH-UHFFFAOYSA-N 0.000 description 1
TVZGACDUOSZQKY-LBPRGKRZSA-N 4-aminofolic acid Chemical compound C1=NC2=NC(N)=NC(N)=C2N=C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 TVZGACDUOSZQKY-LBPRGKRZSA-N 0.000 description 1
JLNMBIKJQAKQBH-UHFFFAOYSA-N 4-cyclohexylaniline Chemical compound C1=CC(N)=CC=C1C1CCCCC1 JLNMBIKJQAKQBH-UHFFFAOYSA-N 0.000 description 1
URAARCWOADCWLA-UHFFFAOYSA-N 4-pyrrolidin-1-ylaniline Chemical compound C1=CC(N)=CC=C1N1CCCC1 URAARCWOADCWLA-UHFFFAOYSA-N 0.000 description 1
125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 description 1
LGZKGOGODCLQHG-CYBMUJFWSA-N 5-[(2r)-2-hydroxy-2-(3,4,5-trimethoxyphenyl)ethyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1C[C@@H](O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-CYBMUJFWSA-N 0.000 description 1
NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
206010000890 Acute myelomonocytic leukaemia Diseases 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
229910000838 Al alloy Inorganic materials 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
244000144730 Amygdalus persica Species 0.000 description 1
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 1
208000031295 Animal disease Diseases 0.000 description 1
108020004491 Antisense DNA Proteins 0.000 description 1
108020005544 Antisense RNA Proteins 0.000 description 1
BFYIZQONLCFLEV-DAELLWKTSA-N Aromasine Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(=C)C2=C1 BFYIZQONLCFLEV-DAELLWKTSA-N 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
206010006187 Breast cancer Diseases 0.000 description 1
208000026310 Breast neoplasm Diseases 0.000 description 1
125000004649 C2-C8 alkynyl group Chemical group 0.000 description 1
LQPFTNGUHVZEMI-UHFFFAOYSA-N CC(C(OC)=O)=C.Br Chemical compound CC(C(OC)=O)=C.Br LQPFTNGUHVZEMI-UHFFFAOYSA-N 0.000 description 1
KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
108090000994 Catalytic RNA Proteins 0.000 description 1
102000053642 Catalytic RNA Human genes 0.000 description 1
241001227713 Chiron Species 0.000 description 1
235000019743 Choline chloride Nutrition 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
208000001333 Colorectal Neoplasms Diseases 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 description 1
108090000695 Cytokines Proteins 0.000 description 1
102000004127 Cytokines Human genes 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
229920002307 Dextran Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
206010012689 Diabetic retinopathy Diseases 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
ZQZFYGIXNQKOAV-OCEACIFDSA-N Droloxifene Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=C(O)C=CC=1)\C1=CC=C(OCCN(C)C)C=C1 ZQZFYGIXNQKOAV-OCEACIFDSA-N 0.000 description 1
206010058314 Dysplasia Diseases 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
208000000461 Esophageal Neoplasms Diseases 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
229940123583 Factor Xa inhibitor Drugs 0.000 description 1
206010016654 Fibrosis Diseases 0.000 description 1
VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 description 1
208000032612 Glial tumor Diseases 0.000 description 1
206010018338 Glioma Diseases 0.000 description 1
206010018364 Glomerulonephritis Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
102000004457 Granulocyte-Macrophage Colony-Stimulating Factor Human genes 0.000 description 1
206010066476 Haematological malignancy Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
101000916644 Homo sapiens Macrophage colony-stimulating factor 1 receptor Proteins 0.000 description 1
101001052849 Homo sapiens Tyrosine-protein kinase Fer Proteins 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-O Htris Chemical compound OCC([NH3+])(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-O 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
206010023421 Kidney fibrosis Diseases 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
239000005551 L01XE03 - Erlotinib Substances 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
GQYIWUVLTXOXAJ-UHFFFAOYSA-N Lomustine Chemical compound ClCCN(N=O)C(=O)NC1CCCCC1 GQYIWUVLTXOXAJ-UHFFFAOYSA-N 0.000 description 1
108060001084 Luciferase Proteins 0.000 description 1
239000005089 Luciferase Substances 0.000 description 1
102100028198 Macrophage colony-stimulating factor 1 receptor Human genes 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
102000016193 Metabotropic glutamate receptors Human genes 0.000 description 1
108010010914 Metabotropic glutamate receptors Proteins 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
102000008300 Mutant Proteins Human genes 0.000 description 1
108010021466 Mutant Proteins Proteins 0.000 description 1
108010083674 Myelin Proteins Proteins 0.000 description 1
102000006386 Myelin Proteins Human genes 0.000 description 1
208000033835 Myelomonocytic Acute Leukemia Diseases 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
241001274216 Naso Species 0.000 description 1
229910000990 Ni alloy Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
KYRVNWMVYQXFEU-UHFFFAOYSA-N Nocodazole Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CS1 KYRVNWMVYQXFEU-UHFFFAOYSA-N 0.000 description 1
AKUFYPLYKXDVAG-UHFFFAOYSA-N O[S+]1C=CC=C1 Chemical compound O[S+]1C=CC=C1 AKUFYPLYKXDVAG-UHFFFAOYSA-N 0.000 description 1
REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
108010038807 Oligopeptides Proteins 0.000 description 1
102000015636 Oligopeptides Human genes 0.000 description 1
108700020796 Oncogene Proteins 0.000 description 1
102000043276 Oncogene Human genes 0.000 description 1
206010061535 Ovarian neoplasm Diseases 0.000 description 1
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
108090000854 Oxidoreductases Proteins 0.000 description 1
206010061902 Pancreatic neoplasm Diseases 0.000 description 1
208000031481 Pathologic Constriction Diseases 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
208000000236 Prostatic Neoplasms Diseases 0.000 description 1
235000006040 Prunus persica var persica Nutrition 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
241000282941 Rangifer tarandus Species 0.000 description 1
208000017442 Retinal disease Diseases 0.000 description 1
206010038923 Retinopathy Diseases 0.000 description 1
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
208000005718 Stomach Neoplasms Diseases 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
229920002253 Tannate Polymers 0.000 description 1
FOCVUCIESVLUNU-UHFFFAOYSA-N Thiotepa Chemical compound C1CN1P(N1CC1)(=S)N1CC1 FOCVUCIESVLUNU-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
102000004243 Tubulin Human genes 0.000 description 1
108090000704 Tubulin Proteins 0.000 description 1
102100024537 Tyrosine-protein kinase Fer Human genes 0.000 description 1
108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 1
102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 1
108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 1
241000280995 Viola pallens Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
GJWAPAVRQYYSTK-UHFFFAOYSA-N [(dimethyl-$l^{3}-silanyl)amino]-dimethylsilicon Chemical compound C[Si](C)N[Si](C)C GJWAPAVRQYYSTK-UHFFFAOYSA-N 0.000 description 1
ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
208000011912 acute myelomonocytic leukemia M4 Diseases 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
208000038018 age-related macular disease Diseases 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000004973 alkali metal peroxides Chemical class 0.000 description 1
150000004974 alkaline earth metal peroxides Chemical class 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
150000001345 alkine derivatives Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005133 alkynyloxy group Chemical group 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229960003896 aminopterin Drugs 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000033115 angiogenesis Effects 0.000 description 1
230000002491 angiogenic effect Effects 0.000 description 1
125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
230000003466 anti-cipated effect Effects 0.000 description 1
229940046836 anti-estrogen Drugs 0.000 description 1
230000001833 anti-estrogenic effect Effects 0.000 description 1
230000003432 anti-folate effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000000340 anti-metabolite Effects 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
230000000692 anti-sense effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
230000010100 anticoagulation Effects 0.000 description 1
229940127074 antifolate Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940100197 antimetabolite Drugs 0.000 description 1
239000002256 antimetabolite Substances 0.000 description 1
229940034982 antineoplastic agent Drugs 0.000 description 1
229940045696 antineoplastic drug podophyllotoxin derivative Drugs 0.000 description 1
229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 description 1
239000003816 antisense DNA Substances 0.000 description 1
230000006907 apoptotic process Effects 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
125000001769 aryl amino group Chemical group 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
229940090047 auto-injector Drugs 0.000 description 1
229960002756 azacitidine Drugs 0.000 description 1
125000003828 azulenyl group Chemical group 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
235000012216 bentonite Nutrition 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000005872 benzooxazolyl group Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
229960000397 bevacizumab Drugs 0.000 description 1
229920000249 biocompatible polymer Polymers 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
229960000074 biopharmaceutical Drugs 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
210000004271 bone marrow stromal cell Anatomy 0.000 description 1
ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
125000005620 boronic acid group Chemical class 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000004227 calcium gluconate Substances 0.000 description 1
235000013927 calcium gluconate Nutrition 0.000 description 1
229960004494 calcium gluconate Drugs 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
229940095643 calcium hydroxide Drugs 0.000 description 1
NEEHYRZPVYRGPP-UHFFFAOYSA-L calcium;2,3,4,5,6-pentahydroxyhexanoate Chemical compound [Ca+2].OCC(O)C(O)C(O)C(O)C([O-])=O.OCC(O)C(O)C(O)C(O)C([O-])=O NEEHYRZPVYRGPP-UHFFFAOYSA-L 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
229940127093 camptothecin Drugs 0.000 description 1
XNRHTMDHGDWBGP-UHFFFAOYSA-N carbamic acid;hydrochloride Chemical compound Cl.NC(O)=O XNRHTMDHGDWBGP-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
YAYRGNWWLMLWJE-UHFFFAOYSA-L carboplatin Chemical compound O=C1O[Pt](N)(N)OC(=O)C11CCC1 YAYRGNWWLMLWJE-UHFFFAOYSA-L 0.000 description 1
229960004562 carboplatin Drugs 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
230000003177 cardiotonic effect Effects 0.000 description 1
201000011529 cardiovascular cancer Diseases 0.000 description 1
XREUEWVEMYWFFA-CSKJXFQVSA-N carminomycin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XREUEWVEMYWFFA-CSKJXFQVSA-N 0.000 description 1
229930188550 carminomycin Natural products 0.000 description 1
XREUEWVEMYWFFA-UHFFFAOYSA-N carminomycin I Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=C(O)C=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XREUEWVEMYWFFA-UHFFFAOYSA-N 0.000 description 1
229950001725 carubicin Drugs 0.000 description 1
230000024245 cell differentiation Effects 0.000 description 1
239000013592 cell lysate Substances 0.000 description 1
230000033077 cellular process Effects 0.000 description 1
230000036755 cellular response Effects 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
MLIFNJABMANKEU-UHFFFAOYSA-N cep-5214 Chemical compound C1=CC=C2C3=C(C(=O)NC4)C4=C(C=4C(=CC=C(C=4)COC(C)C)N4CCCO)C4=C3CC2=C1 MLIFNJABMANKEU-UHFFFAOYSA-N 0.000 description 1
229960005395 cetuximab Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
230000035572 chemosensitivity Effects 0.000 description 1
238000004296 chiral HPLC Methods 0.000 description 1
JCKYGMPEJWAADB-UHFFFAOYSA-N chlorambucil Chemical compound OC(=O)CCCC1=CC=C(N(CCCl)CCCl)C=C1 JCKYGMPEJWAADB-UHFFFAOYSA-N 0.000 description 1
229960004630 chlorambucil Drugs 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
229960003178 choline chloride Drugs 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
230000004087 circulation Effects 0.000 description 1
WDDPHFBMKLOVOX-AYQXTPAHSA-N clofarabine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1F WDDPHFBMKLOVOX-AYQXTPAHSA-N 0.000 description 1
229960000928 clofarabine Drugs 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
229960001338 colchicine Drugs 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
LGZKGOGODCLQHG-UHFFFAOYSA-N combretastatin Natural products C1=C(O)C(OC)=CC=C1CC(O)C1=CC(OC)=C(OC)C(OC)=C1 LGZKGOGODCLQHG-UHFFFAOYSA-N 0.000 description 1
239000003184 complementary RNA Substances 0.000 description 1
239000002131 composite material Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
230000001268 conjugating effect Effects 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
230000006552 constitutive activation Effects 0.000 description 1
239000000599 controlled substance Substances 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229940099112 cornstarch Drugs 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
KTHXBEHDVMTNOH-UHFFFAOYSA-N cyclobutanol Chemical compound OC1CCC1 KTHXBEHDVMTNOH-UHFFFAOYSA-N 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
239000002254 cytotoxic agent Substances 0.000 description 1
231100000599 cytotoxic agent Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
230000010013 cytotoxic mechanism Effects 0.000 description 1
231100000263 cytotoxicity test Toxicity 0.000 description 1
238000007405 data analysis Methods 0.000 description 1
125000005508 decahydronaphthalenyl group Chemical group 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000001934 delay Effects 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000007933 dermal patch Substances 0.000 description 1
ACYGYJFTZSAZKR-UHFFFAOYSA-J dicalcium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Ca+2].[Ca+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O ACYGYJFTZSAZKR-UHFFFAOYSA-J 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 description 1
125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
239000001177 diphosphate Substances 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 description 1
VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 description 1
239000003534 dna topoisomerase inhibitor Substances 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
229950004203 droloxifene Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
239000000975 dye Substances 0.000 description 1
229940009662 edetate Drugs 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000003821 enantio-separation Methods 0.000 description 1
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
AAKJLRGGTJKAMG-UHFFFAOYSA-N erlotinib Chemical compound C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 AAKJLRGGTJKAMG-UHFFFAOYSA-N 0.000 description 1
229960001433 erlotinib Drugs 0.000 description 1
229950000206 estolate Drugs 0.000 description 1
239000000328 estrogen antagonist Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
229960000255 exemestane Drugs 0.000 description 1
208000030533 eye disease Diseases 0.000 description 1
239000004744 fabric Substances 0.000 description 1
230000004761 fibrosis Effects 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000020375 flavoured syrup Nutrition 0.000 description 1
238000009408 flooring Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
238000002875 fluorescence polarization Methods 0.000 description 1
201000005206 focal segmental glomerulosclerosis Diseases 0.000 description 1
239000004052 folic acid antagonist Substances 0.000 description 1
VVIAGPKUTFNRDU-ABLWVSNPSA-N folinic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-ABLWVSNPSA-N 0.000 description 1
235000008191 folinic acid Nutrition 0.000 description 1
239000011672 folinic acid Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
229960002258 fulvestrant Drugs 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000000499 gel Substances 0.000 description 1
206010061989 glomerulosclerosis Diseases 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
239000003825 glutamate receptor antagonist Substances 0.000 description 1
125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229930182470 glycoside Natural products 0.000 description 1
150000002338 glycosides Chemical class 0.000 description 1
239000003979 granulating agent Substances 0.000 description 1
230000003394 haemopoietic effect Effects 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000036541 health Effects 0.000 description 1
208000014951 hematologic disease Diseases 0.000 description 1
230000009033 hematopoietic malignancy Effects 0.000 description 1
210000003958 hematopoietic stem cell Anatomy 0.000 description 1
125000000455 heteroaryl-fused-cycloalkyl group Chemical group 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XHJJEWBMBSQVCJ-UHFFFAOYSA-N homocamfin Chemical compound CC(C)C1CC(C)=CC(=O)C1 XHJJEWBMBSQVCJ-UHFFFAOYSA-N 0.000 description 1
229950007035 homocamfin Drugs 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
XGIHQYAWBCFNPY-AZOCGYLKSA-N hydrabamine Chemical compound C([C@@H]12)CC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC[C@@]1(C)CNCCNC[C@@]1(C)[C@@H]2CCC3=CC(C(C)C)=CC=C3[C@@]2(C)CCC1 XGIHQYAWBCFNPY-AZOCGYLKSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
DQKGOGJIOHUEGK-UHFFFAOYSA-M hydron;2-hydroxyethyl(trimethyl)azanium;carbonate Chemical compound OC([O-])=O.C[N+](C)(C)CCO DQKGOGJIOHUEGK-UHFFFAOYSA-M 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
206010020718 hyperplasia Diseases 0.000 description 1
229940075628 hypomethylating agent Drugs 0.000 description 1
229960000908 idarubicin Drugs 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
239000012729 immediate-release (IR) formulation Substances 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
208000014674 injury Diseases 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000007913 intrathecal administration Methods 0.000 description 1
230000002601 intratumoral effect Effects 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229940043355 kinase inhibitor Drugs 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
JYTUSYBCFIZPBE-AMTLMPIISA-M lactobionate Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-M 0.000 description 1
229940099584 lactobionate Drugs 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229950001845 lestaurtinib Drugs 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
229960003881 letrozole Drugs 0.000 description 1
HPJKCIUCZWXJDR-UHFFFAOYSA-N letrozole Chemical compound C1=CC(C#N)=CC=C1C(N1N=CN=C1)C1=CC=C(C#N)C=C1 HPJKCIUCZWXJDR-UHFFFAOYSA-N 0.000 description 1
229960001691 leucovorin Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
229960002247 lomustine Drugs 0.000 description 1
208000020816 lung neoplasm Diseases 0.000 description 1
210000003738 lymphoid progenitor cell Anatomy 0.000 description 1
210000003563 lymphoid tissue Anatomy 0.000 description 1
208000002780 macular degeneration Diseases 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
230000036210 malignancy Effects 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
229960003194 meglumine Drugs 0.000 description 1
239000012528 membrane Substances 0.000 description 1
108020004999 messenger RNA Proteins 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229960000485 methotrexate Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
230000004089 microcirculation Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
231100000324 minimal toxicity Toxicity 0.000 description 1
229960004857 mitomycin Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000003990 molecular pathway Effects 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
210000005012 myelin Anatomy 0.000 description 1
210000003643 myeloid progenitor cell Anatomy 0.000 description 1
230000002071 myeloproliferative effect Effects 0.000 description 1
DDBRXOJCLVGHLX-UHFFFAOYSA-N n,n-dimethylmethanamine;propane Chemical class CCC.CN(C)C DDBRXOJCLVGHLX-UHFFFAOYSA-N 0.000 description 1
LBWFXVZLPYTWQI-IPOVEDGCSA-N n-[2-(diethylamino)ethyl]-5-[(z)-(5-fluoro-2-oxo-1h-indol-3-ylidene)methyl]-2,4-dimethyl-1h-pyrrole-3-carboxamide;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C LBWFXVZLPYTWQI-IPOVEDGCSA-N 0.000 description 1
XFKCWRFSPKYBHR-UHFFFAOYSA-N n-methylmethanamine;propane Chemical class CCC.CNC XFKCWRFSPKYBHR-UHFFFAOYSA-N 0.000 description 1
YEHOJHBOXFZFCW-UHFFFAOYSA-N n-piperidin-4-ylpyrimidin-4-amine Chemical compound C1CNCCC1NC1=CC=NC=N1 YEHOJHBOXFZFCW-UHFFFAOYSA-N 0.000 description 1
239000002105 nanoparticle Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229920001206 natural gum Polymers 0.000 description 1
230000001338 necrotic effect Effects 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
230000006715 negative regulation of smooth muscle cell proliferation Effects 0.000 description 1
210000005170 neoplastic cell Anatomy 0.000 description 1
210000000885 nephron Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
229950006344 nocodazole Drugs 0.000 description 1
231100000065 noncytotoxic Toxicity 0.000 description 1
230000002020 noncytotoxic effect Effects 0.000 description 1
238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
230000002018 overexpression Effects 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
DWAFYCQODLXJNR-BNTLRKBRSA-L oxaliplatin Chemical compound O1C(=O)C(=O)O[Pt]11N[C@@H]2CCCC[C@H]2N1 DWAFYCQODLXJNR-BNTLRKBRSA-L 0.000 description 1
229960001756 oxaliplatin Drugs 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
229940014662 pantothenate Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
WBXPDJSOTKVWSJ-ZDUSSCGKSA-N pemetrexed Chemical compound C=1NC=2NC(N)=NC(=O)C=2C=1CCC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 WBXPDJSOTKVWSJ-ZDUSSCGKSA-N 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
230000035515 penetration Effects 0.000 description 1
235000019371 penicillin G benzathine Nutrition 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
229960002087 pertuzumab Drugs 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
238000001050 pharmacotherapy Methods 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
125000001095 phosphatidyl group Chemical group 0.000 description 1
229940067605 phosphatidylethanolamines Drugs 0.000 description 1
150000008104 phosphatidylethanolamines Chemical class 0.000 description 1
150000004713 phosphodiesters Chemical class 0.000 description 1
239000003757 phosphotransferase inhibitor Substances 0.000 description 1
DCWXELXMIBXGTH-UHFFFAOYSA-N phosphotyrosine Chemical compound OC(=O)C(N)CC1=CC=C(OP(O)(O)=O)C=C1 DCWXELXMIBXGTH-UHFFFAOYSA-N 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
IWELDVXSEVIIGI-UHFFFAOYSA-N piperazin-2-one Chemical class O=C1CNCCN1 IWELDVXSEVIIGI-UHFFFAOYSA-N 0.000 description 1
YJGVMLPVUAXIQN-XVVDYKMHSA-N podophyllotoxin Chemical class COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-XVVDYKMHSA-N 0.000 description 1
239000003600 podophyllotoxin derivative Substances 0.000 description 1
229920000128 polypyrrole Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
238000010837 poor prognosis Methods 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
238000004321 preservation Methods 0.000 description 1
201000008171 proliferative glomerulonephritis Diseases 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
239000003909 protein kinase inhibitor Substances 0.000 description 1
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
208000005069 pulmonary fibrosis Diseases 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
YMXFJTUQQVLJEN-UHFFFAOYSA-N pyrimidine Chemical compound C1=CN=CN=C1.C1=CN=CN=C1 YMXFJTUQQVLJEN-UHFFFAOYSA-N 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
229960004622 raloxifene Drugs 0.000 description 1
GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
108091092562 ribozyme Proteins 0.000 description 1
229960004641 rituximab Drugs 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
201000000980 schizophrenia Diseases 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000849 selective androgen receptor modulator Substances 0.000 description 1
238000010956 selective crystallization Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
238000003153 stable transfection Methods 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
229910000080 stannane Inorganic materials 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000036262 stenosis Effects 0.000 description 1
208000037804 stenosis Diseases 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
WPLOVIFNBMNBPD-ATHMIXSHSA-N subtilin Chemical compound CC1SCC(NC2=O)C(=O)NC(CC(N)=O)C(=O)NC(C(=O)NC(CCCCN)C(=O)NC(C(C)CC)C(=O)NC(=C)C(=O)NC(CCCCN)C(O)=O)CSC(C)C2NC(=O)C(CC(C)C)NC(=O)C1NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C1NC(=O)C(=C/C)/NC(=O)C(CCC(N)=O)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)CNC(=O)C(NC(=O)C(NC(=O)C2NC(=O)CNC(=O)C3CCCN3C(=O)C(NC(=O)C3NC(=O)C(CC(C)C)NC(=O)C(=C)NC(=O)C(CCC(O)=O)NC(=O)C(NC(=O)C(CCCCN)NC(=O)C(N)CC=4C5=CC=CC=C5NC=4)CSC3)C(C)SC2)C(C)C)C(C)SC1)CC1=CC=CC=C1 WPLOVIFNBMNBPD-ATHMIXSHSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
WINHZLLDWRZWRT-ATVHPVEESA-N sunitinib Chemical compound CCN(CC)CCNC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C WINHZLLDWRZWRT-ATVHPVEESA-N 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
230000008409 synovial inflammation Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
229950002757 teoclate Drugs 0.000 description 1
CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 1
DQQJBEAXSOOCPG-UHFFFAOYSA-N tert-butyl n-pyrrolidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNC1 DQQJBEAXSOOCPG-UHFFFAOYSA-N 0.000 description 1
GARSDLRPRBEKQE-UHFFFAOYSA-N tert-butyl(pyrrolidin-3-yl)carbamic acid Chemical compound CC(C)(C)N(C(O)=O)C1CCNC1 GARSDLRPRBEKQE-UHFFFAOYSA-N 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
229960001196 thiotepa Drugs 0.000 description 1
125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229940044693 topoisomerase inhibitor Drugs 0.000 description 1
229960005026 toremifene Drugs 0.000 description 1
XFCLJVABOIYOMF-QPLCGJKRSA-N toremifene Chemical compound C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(\CCCl)C1=CC=CC=C1 XFCLJVABOIYOMF-QPLCGJKRSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
238000010361 transduction Methods 0.000 description 1
230000026683 transduction Effects 0.000 description 1
238000001890 transfection Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000013519 translation Methods 0.000 description 1
230000005945 translocation Effects 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
230000008733 trauma Effects 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
210000003556 vascular endothelial cell Anatomy 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229930195724 β-lactose Natural products 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Hematology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Materials For Medical Uses (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

BRPI0613644-3A 2005-06-10 2006-06-07 moduladores de tieno pirimidina e tieno pirimidina cinase BRPI0613644A2 (pt)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US68971005P	2005-06-10	2005-06-10
US60/689,710		2005-06-10
US74694106P	2006-05-10	2006-05-10
US60/746,941		2006-05-10
PCT/US2006/022151 WO2006135639A1 (en)	2005-06-10	2006-06-07	Thiξnopyrimidine and thienopyridine derivatives as flt-3 kinase inhibitors

Publications (1)

Publication Number	Publication Date
BRPI0613644A2 true BRPI0613644A2 (pt)	2011-01-25

Family

ID=37074647

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BRPI0613644-3A BRPI0613644A2 (pt)	2005-06-10	2006-06-07	moduladores de tieno pirimidina e tieno pirimidina cinase

Country Status (19)

Country	Link
US (3)	US20060281768A1 (es)
EP (1)	EP1899355A1 (es)
JP (1)	JP2008543759A (es)
KR (1)	KR20080021126A (es)
AR (1)	AR057063A1 (es)
AU (1)	AU2006258049A1 (es)
BR (1)	BRPI0613644A2 (es)
CA (1)	CA2611587A1 (es)
CR (1)	CR9650A (es)
EA (1)	EA200800011A1 (es)
EC (1)	ECSP077992A (es)
IL (1)	IL187689A0 (es)
MX (1)	MX2007015741A (es)
NI (1)	NI200700311A (es)
NO (1)	NO20080162L (es)
PE (1)	PE20070070A1 (es)
TW (1)	TW200716651A (es)
UY (1)	UY29590A1 (es)
WO (1)	WO2006135639A1 (es)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MY179032A (en)	2004-10-25	2020-10-26	Cancer Research Tech Ltd	Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors
JP2009534454A (ja) *	2006-04-25	2009-09-24	アステックス、セラピューティックス、リミテッド	医薬化合物
WO2007125321A2 (en)	2006-04-25	2007-11-08	Astex Therapeutics Limited	Purine and deazapurine derivatives as pharmaceutical compounds
EP2066642A1 (en) *	2006-09-25	2009-06-10	Arete Therapeutics, INC.	Soluble epoxide hydrolase inhibitors
TW200924781A (en)	2007-09-14	2009-06-16	Janssen Pharmaceutica Nv	Thieno- and furo-pyrimidine modulators of the histamine H4 receptor
PL2201012T3 (pl)	2007-10-11	2014-11-28	Astrazeneca Ab	Pochodne pirolo[2,3-d]pirymidyny jako inhibitory kinazy białkowej b
EP2694056B1 (en)	2011-04-01	2019-10-16	AstraZeneca AB	Therapeutic treatment
AU2012256237B2 (en)	2011-05-13	2017-01-05	Array Biopharma Inc.	Pyrrolidinyl urea and pyrrolidinyl thiourea compounds as TrkA kinase inhibitors
AR090037A1 (es) *	2011-11-15	2014-10-15	Xention Ltd	Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio
PH12014500943A1 (en)	2011-11-30	2014-06-30	Astrazeneca Ab	Combination treatment of cancer
AU2013204533B2 (en)	2012-04-17	2017-02-02	Astrazeneca Ab	Crystalline forms
CA2949160C (en)	2014-05-15	2023-03-21	Array Biopharma Inc.	1-((3s,4r)-4-(3-fluorophenyl)-1-(2-methoxyethyl)pyrrolidin-3-yl)-3-(4-methyl-3-(2-methylpyrimidin-5-yl)-1-phenyl-1h-pyrazol-5-yl)urea as a trka kinase inhibitor
US10806737B2 (en)	2016-12-23	2020-10-20	Arvinas Operations, Inc.	Compounds and methods for the targeted degradation of fetal liver kinase polypeptides
KR101954370B1 (ko)	2018-07-25	2019-03-05	한미약품 주식회사	피리미딘 화합물 및 이를 포함하는 암의 예방 또는 치료용 약학 조성물
ES2974634T3 (es)	2018-12-21	2024-06-28	Celgene Corp	Inhibidores de tienopiridinas de RIPK2
PH12021551985A1 (en)	2019-02-22	2022-08-22	Hanmi Pharmaceutical Co Ltd	Pharmaceutical composition comprising flt3 inhibitor and hypomethylating agent for treating acute myeloid leukemia
EA202290154A1 (ru)	2019-06-27	2022-03-29	Ханми Фарм. Ко., Лтд.	Фармацевтическая композиция для лечения острого миелоидного лейкоза, содержащая ингибитор flt3 и химиотерапевтические агенты
EP4719355A1 (en) *	2023-05-31	2026-04-08	Hanmi Pharm. Co., Ltd.	Solid dispersion of myeloid kinome inhibitors and pharmaceutical composition comprising the same

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1306095A3 (en) *	1992-03-05	2003-06-25	Board Of Regents, The University Of Texas System	Methods and compositions for targeting the vasculature of solid tumors
US5474765A (en) *	1992-03-23	1995-12-12	Ut Sw Medical Ctr At Dallas	Preparation and use of steroid-polyanionic polymer-based conjugates targeted to vascular endothelial cells
US5932765A (en) *	1997-05-23	1999-08-03	Merck Patent Gesellschaft Mit	Nitromethyl ketones, process for preparing them and compositions containing them
CA2309690A1 (en) *	1997-11-11	1999-05-20	Pfizer Products Inc.	Thienopyrimidine and thienopyridine derivatives useful as anticancer agents
TR200002182T2 (tr) *	1998-01-27	2000-12-21	Aventis Pharmaceuticals Products Inc.	İkame edilmiş aksozaherosayklil faktör xa inhibitörleri
EP1179541B1 (en) *	1999-04-28	2004-06-16	Board Of Regents, The University Of Texas System	Compositions and methods for cancer treatment by selectively inhibiting VEGF
US6776796B2 (en) *	2000-05-12	2004-08-17	Cordis Corportation	Antiinflammatory drug and delivery device
DE10110750A1 (de) *	2001-03-07	2002-09-12	Bayer Ag	Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften
AR035885A1 (es) *	2001-05-14	2004-07-21	Novartis Ag	Derivados de 4-amino-5-fenil-7-ciclobutilpirrolo (2,3-d)pirimidina, un proceso para su preparacion, una composicion farmaceutica y el uso de dichos derivados para la preparacion de una composicion farmaceutica
US7105505B2 (en) *	2002-04-18	2006-09-12	Schering Corporation	Benzimidazole derivatives useful as histamine H3 antagonists
MY141867A (en) *	2002-06-20	2010-07-16	Vertex Pharma	Substituted pyrimidines useful as protein kinase inhibitors
BR0313405A (pt) *	2002-08-12	2005-07-12	Takeda Pharmaceutical	Compostos, métodos para preparar um composto e para prevenir e/ou tratar câncer, prodroga, medicamento, modulador do receptor de androgênio, agente para prevenir e/ou tratar hipogonadismo ou pertubação climatérica masculina, osteoporose e câncer, e, uso de um composto
AU2003280599A1 (en) *	2002-10-29	2004-05-25	Kirin Beer Kabushiki Kaisha	QUINOLINE DERIVATIVES AND QUINAZOLINE DERIVATIVES INHIBITING AUTOPHOSPHORYLATION OF Flt3 AND MEDICINAL COMPOSITIONS CONTAINING THE SAME
US20050026944A1 (en) *	2003-07-24	2005-02-03	Patrick Betschmann	Thienopyridine and furopyridine kinase inhibitors
US20060281769A1 (en) *	2005-06-10	2006-12-14	Baumann Christian A	Synergistic modulation of flt3 kinase using thienopyrimidine and thienopyridine kinase modulators

2006
- 2006-06-06 US US11/422,359 patent/US20060281768A1/en not_active Abandoned
- 2006-06-07 AU AU2006258049A patent/AU2006258049A1/en not_active Abandoned
- 2006-06-07 KR KR1020087000618A patent/KR20080021126A/ko not_active Withdrawn
- 2006-06-07 WO PCT/US2006/022151 patent/WO2006135639A1/en not_active Ceased
- 2006-06-07 CA CA002611587A patent/CA2611587A1/en not_active Abandoned
- 2006-06-07 BR BRPI0613644-3A patent/BRPI0613644A2/pt not_active Application Discontinuation
- 2006-06-07 EA EA200800011A patent/EA200800011A1/ru unknown
- 2006-06-07 EP EP06772445A patent/EP1899355A1/en not_active Withdrawn
- 2006-06-07 JP JP2008515879A patent/JP2008543759A/ja not_active Withdrawn
- 2006-06-07 MX MX2007015741A patent/MX2007015741A/es unknown
- 2006-06-07 NI NI200700311A patent/NI200700311A/es unknown
- 2006-06-08 PE PE2006000640A patent/PE20070070A1/es not_active Application Discontinuation
- 2006-06-08 UY UY29590A patent/UY29590A1/es unknown
- 2006-06-09 AR ARP060102425A patent/AR057063A1/es not_active Application Discontinuation
- 2006-06-09 TW TW095120482A patent/TW200716651A/zh unknown
2007
- 2007-11-27 IL IL187689A patent/IL187689A0/en unknown
- 2007-12-10 EC EC2007007992A patent/ECSP077992A/es unknown
2008
- 2008-01-09 CR CR9650A patent/CR9650A/es not_active Application Discontinuation
- 2008-01-09 NO NO20080162A patent/NO20080162L/no not_active Application Discontinuation
2009
- 2009-01-30 US US12/362,933 patent/US20090143378A1/en not_active Abandoned
- 2009-01-30 US US12/363,043 patent/US20090163710A1/en not_active Abandoned

Also Published As

Publication number	Publication date
WO2006135639A1 (en)	2006-12-21
UY29590A1 (es)	2006-10-02
NO20080162L (no)	2008-03-07
AU2006258049A1 (en)	2006-12-21
US20060281768A1 (en)	2006-12-14
PE20070070A1 (es)	2007-03-08
AU2006258049A8 (en)	2006-12-21
IL187689A0 (en)	2008-08-07
EP1899355A1 (en)	2008-03-19
ECSP077992A (es)	2008-01-23
AR057063A1 (es)	2007-11-14
NI200700311A (es)	2009-03-03
EA200800011A1 (ru)	2008-06-30
CA2611587A1 (en)	2006-12-21
US20090143378A1 (en)	2009-06-04
KR20080021126A (ko)	2008-03-06
MX2007015741A (es)	2008-04-29
TW200716651A (en)	2007-05-01
CR9650A (es)	2008-09-09
US20090163710A1 (en)	2009-06-25
JP2008543759A (ja)	2008-12-04

Legal Events

Date

Code

Title

Description

2011-02-22

B25A

Requested transfer of rights approved

Owner name: JOHNSON AND JOHNSON (US)

Free format text: TRANSFERIDO DE: JANSSEN PHARMACEUTICA N.V.

2011-07-26

B11A

Dismissal acc. art.33 of ipl - examination not requested within 36 months of filing

2011-11-01

B11Y

Definitive dismissal - extension of time limit for request of examination expired [chapter 11.1.1 patent gazette]

Publication	Publication Date	Title
JP7260723B2 (ja)	2023-04-18	ＨＥＲ２阻害薬としての［１，３］ジアジノ［５，４－ｄ］ピリミジン
ES2981592T3 (es)	2024-10-09	Derivados de 6-(4-amino-3-metil-2-oxa-8-azaespiro[4.5]decan-8-il)-3-(2,3-diclorofenil)-2-metilpirimidin-4(3H)-ona y compuestos relacionados como inhibidores de PTPN11 (SHP2) para tratar el cáncer
ES2360933T3 (es)	2011-06-10	Derivados de heteroarilo condensados.
CN104903321B (zh)	2017-10-24	作为激酶抑制剂的经取代三环苯并咪唑
EP4214209A1 (en)	2023-07-26	Indole derivatives as ras inhibitors in the treatment of cancer
US20090163710A1 (en)	2009-06-25	Thienopyrimidine and thienopyridine kinase modulators
JPWO2015022926A1 (ja)	2017-03-02	新規な縮合ピリミジン化合物又はその塩
BRPI0611621A2 (pt)	2010-09-21	moduladores de aminoquinolina e aminoquinazolina cinase
WO2021043208A1 (en)	2021-03-11	3, 5-disubstituted pyrazole compounds as kinase inhibitors and uses thereof
ES2319574T3 (es)	2009-05-08	Aminopirimidinas como moduladores de quinasa.
ES2367760T3 (es)	2011-11-08	Derivados de quinazolinona como inhibidores de la polimerización de la tubulina.
JP2008543760A (ja)	2008-12-04	キナーゼモジュレーターとしてのアミノピリミジン
JP2024513538A (ja)	2024-03-25	Ｐａｒｐ阻害剤としての置換融合二環式化合物及びその使用
WO2023185073A1 (zh)	2023-10-05	Parp7抑制剂及其用途
JPWO2019131794A1 (ja)	2020-12-24	抗がん剤
TWI913256B (zh)	2026-02-01	作為ＨＥＲ２抑制劑之[１,３]二基[５,４-ｄ]嘧啶
BR112019020309A2 (pt)	2020-04-28	derivados de quinoxalina e piridopirazina como inibidores de pi3k-beta
EP4673448A1 (en)	2026-01-07	Substituted nitrogen-containing tricyclic compounds as parp inhibitors and the use thereof
CN121627671A (zh)	2026-03-10	靶向Polθ的乙烯基磺酰基取代的化合物及其应用
KR20260053572A (ko)	2026-04-21	암의 치료에서 ras 억제제로서 인돌 유도체
HK1116059B (en)	2009-09-25	Aminopyrimidines as kinase modulators